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Mistakes That Made Them: Missteps of Famous Entrepreneurs

Deborah Sweeney
Deborah Sweeney

When we think of the most famous CEOs of our time, we think of them as perfect, untouchable examples of how to run a business.

But even the big dogs make mistakes.

Sometimes, those “mistakes” can be what makes a career.

Here are three of the most successful entrepreneurs of our time and the mistakes they made that defined their businesses:

Related Article: You’re Not an Entrepreneur (Yet), and That’s Okay

Richard Branson Thumbs Up

Richard Branson

We all know Richard Branson for his extensive and timeless Virgin brand. He’s been someone to look to as a company culture visionary and an expert in creating a sense of longevity in a company.

Branson had his first business venture at the age of 16, when he created a magazine called, “Student.” From there, he set up his first mail-order record business. Taking a liking to the record business, in 1972 he opened a chain of record stores: Virgin Records (later known as Virgin Megastores). Though, it wasn’t until the 80s that the Virgin brand really began to take off with the expansion of Virgin Atlantic and Virgin Records Music Label.

However, between everything he’s done, with every company he’s started and each venture he’s expanded, there certainly were a couple failures that helped to define this famous CEO.

In 1994, Branson tried expanding the brand with a couple Virgin signature drinks. A few of them being: Virgin Cola, Virgin Vodka, Virgin Vines, Virgin Energy Shot, and Virgin Ooze (an alcoholic beverage). Though, as you can see by the lack of Virgin beverages in stores and bars, the drinks didn’t take off. But it’s these new, inventive ideas that make Branson who he is. Branson is not one to shy away from an off-the-wall idea just to give it a try. Making a move like this in 1994 helped pave the way for running his brand with a sense of nonconformist innovation.      

As of 2015, Forbes lists Branson’s net worth at about $5 billion.

Reed Hastings

Reed Hastings

Netflix has become much more than a movie and TV show watching service- it’s become a part of our culture. Reed Hastings Co-founded Netflix in 1997, and, today, is the CEO. Hastings started Netflix because he owed a crazy late fee of $40 for a movie he had yet to return to the video store. He realized that a gym membership had a much more effective business model- customers could work out as much or as little as they wanted while paying a flat fee each month.

Netflix is such a huge part of our lives now; Hasting’s biggest mistake almost seems irrelevant now. But in July 2011, Netflix announced that their subscription prices would be changing and that the streaming service would now be charged. Initially, the move lost the company a lot of business. Customers canceled their memberships, and stock prices went down. Without much competition, and with such a good understanding of adjusting to what customers want, customers came back around sooner rather than later. Streaming is now the only way to go- and it’s celebrated, but there was a little bit there where the whole thing was considered a huge mistake on Hastings’ part. Now, that “mistake” made the company what it is today.

Today, his net worth is estimated to be $1.6 billion.

Related Article: The Top 10 Qualities That Define An Entrepreneur

Tim Cook and Steve Jobs

Tim Cook

Though he’s no Steve Jobs, Tim Cook has become an integral part of Apple. Tim Cook joined Apple in 1998 as Senior VP of worldwide operations, as well as Executive VP of worldwide sales and operations and Chief Operating Officer before being named CEO in 2011, succeeding Steve Jobs.

Before Apple, Cook spent 12 years at IBM as the Director of North American Fulfillment. After that, he was the COO for the computer reseller division of Intelligent Electronics, and VP for corporate materials at Compaq. In 1998, he was asked to Join Apple by Jobs. Though Cook has been questioned about the major changes he made to the company’s executive team, the thing that he was probably most criticized for was the Apple Maps mistake.

With that fateful iOS 6 update in 2012, Maps received an almost unanimous negative review from the public. The app lacked major destinations, gave inaccurate directions, and involved a confusing replacement of native transit directions with third-party routing apps. Many thought it looked like the update came out before they were ready; it looked sloppy, and Cook was largely blamed.

Though, at the time, Apple received a lot of criticism, they recovered just fine on a large scale. Pushing an app before its bugs are fixed is indeed a mistake, but it is this thinking (pushing on ahead before being completely ready) that’s made Apple the ahead-of-the-curve company it is today. Apple has always been at the front of the technological revolution, perhaps they wouldn’t be if they had always “waited until they were ready.”

His net worth is estimated to be $785 million.

Image Credit: Fizkes / Getty Images
Deborah Sweeney
Deborah Sweeney Member
Deborah Sweeney is the CEO of MyCorporation is a leader in online legal filing services for entrepreneurs and businesses, providing start-up bundles that include corporation and LLC formation, registered agent, DBA, and trademark & copyright filing services. MyCorporation does all the work, making the business formation and maintenance quick and painless, so business owners can focus on what they do best. Follow her on Google+ and on Twitter @deborahsweeney and @mycorporation.